AdQuick co-founder and CEO Matt O’Connor came to the University of Virginia’s Darden School of Business to learn how to make his entrepreneurial vision into a reality.

Things didn’t work out as planned.

O’Connor’s plans for Footprint Free, a business combining elements of a Zagat-esque rating service with steps to help small businesses lessen their carbon footprint, never became a viable business, although a summer spent in the Darden Business Incubator (now known as the i.Lab Incubator) sharpened his approach to venture creation.

The experience also helped seed the idea for his subsequent company, when the seemingly simple act of attempting to purchase a billboard proved maddeningly complex.

“It was a bizarrely opaque process with no single place to go,” the 2013 Darden graduate said. “It was a really, really frustrating experience.”

The experience stuck with O’Connor as he put his startup dreams on hold and took a positon with Instacart, the grocery delivery service that was in the early stages of an aggressive expansion campaign.

O’Connor worked at the company for two years, helping Instacart – which was recently valued at $3.4 billion – push into new markets as it went through a period of rapid growth and capital raising.

“After learning how to take something from concept to a little bit of revenue, but without external funding, Instacart was perfect because it was at that next stage, where it had a concept, had some external funding, and then we had to figure out how to scale it up and how to turn it profitable,” O’Connor said. “So it was really helpful to look at that next stage in a tech company’s lifecycle.”

The experience also reiterated the previous lesson of the difficulty in purchasing outdoor advertising.

When the tech-centric delivery service expanded to a new market, O’Connor would again attempt to purchase a billboard and again find himself at the mercy of sales reps, spreadsheets and PDFs.

O’Connor knew he could build a better system and began to formulate a plan to bring outdoor advertising into the 21st century. His work at Instacart left him confident that the technology to build a vastly improved buying system was well within his grasp, and a subsequent meeting with the former head of CBS Outdoor convinced him that sellers would also be amenable to the product.

“I thought if someone on the side I didn’t know, the billboard company side, was bullish on it, then I was convinced,” O’Connor said. “I started to line up a co-founder, figured out where and how to start it, and just started doing it.”

The tangible realization of the company meant that when Amazon, which had hired O’Connor to help get its Amazon Flex independent contracting service off the ground, offered a new role at the company, O’Connor decided it was instead time to fully commit to AdQuick.

O’Connor set up shop in Los Angeles – “the billboard capital of the world” – and began the process of connecting outdoor advertising buyers and sellers. The company functions not unlike a travel search engine, with buyers able to see all of the available inventory of outdoor advertising in a designated geography, with detailed breakdowns on attributes like traffic and demographics, as well as pricing.

The company also promises the sort of measurability and metrics that advertisers have come to expect from digital platforms, using a multitude of data sources to track impressions and, ultimately, return on investment. O’Connor said the company is able to measure what percentage of consumers exposed to an ad ultimately end up setting foot in the related brick-and-mortar store, for instance.

“We’ve got seven or eight different kinds of data integrations that allow us to tell marketers how well their campaign actually works,” O’Connor said. “And because more and more data is being created in the real world, it’s becoming a more and more measurable medium.”

Although he serves as CEO, leading the seven-person company often means wearing multiple hats. O’Connor said the “cross-functionality” of his Darden education comes into play when day-to-day leadership often simply means being the “pinch hitter” and doing what needs to be done. O’Connor said he’s often the one running the data analysis, for instance, and credits Darden professor emeritus Phil Pfeifer for helping him know what to look for in the numbers.

“I feel like I put people in positions that accentuate their strengths and figure out where our weaknesses are as a team and try to plug those for an interim gap until we can hire,” O’Connor said. “As a resource-constrained team, we also have to keep an eye out for when we will need more capital and what that timeline looks like and how we get to those milestones.”

The startup has received initial votes of confidence from high-profile funders, receiving $1.1 million in seed funding from groups led by Reddit co-founder and UVA alumnus Alexis Ohanian’s Initialized Capital. In a blog post, Ohanian said the concept “resonated with me immediately.” While he had seen other entrants attempting to disrupt the growing billboard advertising market Ohanian said, “AdQuick was the first of these companies promising that future who actually delivered a quality software product in the present.”

O’Connor has also hooked up with elements of the Darden network. He meets regularly with T.R. Harrington, a 2004 Darden graduate and a member of the Batten Institute for Entrepreneurship and Innovation advisory council, whose agency, Darwin Marketing, helped pioneer digital marketing in China.

“Having started an ad agency myself in China, I felt like I could provide some lessons and support to help Matt and AdQuick navigate their journey,” Harrington said. “Modern marketing demands data and ROI and AdQuick is bringing just that to the archaic, $40 billion global outdoor advertising space.”

A little more than a year into the venture, O’Connor describes himself as “cautiously optimistic,” with a viable product, successful case studies and a growing network of buyers and sellers.

“We have a long way to go, but as compared to our forecast and where we thought we would be, we’re a couple of years ahead of schedule,” O’Connor said. “We were profitable last month, which we didn’t expect until 2019. We’re doing great, but there’s a long way to go.”

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